This invention relates to oxyoxetanes and more particularly to 3-hydroxyoxetane.
3-Hydroxyoxetane has been prepared previously by a sequence of reactions based on the chlorination of allyl alcohol with chlorine (Wojtowicz, J. A.; Polak, R. J.; Zaslowsky, J. A. J. Org. Chem. 1971, 38, 2061) or with t-butyl hypochlorite (Emling, B. L.; Vogt, R. R.; Hennion, C. G. J. Am. Chem. Soc. 1941, 63, 1624) to give a low yield of 2-allyloxy-3-chloropropanol. The 2-allyloxy-3-chloro-propanol was then treated with sodium hydroxide to give 3-allyloxyoxetane. The olefin portion of the 3-allyloxyoxetane was isomerized with potassium t-butoxide in dimethyl sulfoxide, and 3-hydroxyoxetane was then liberated by hydrolyzing off the olefin group using an acid catalyst in aqueous methanol. However, it would be desirable to find a more efficient method of producing 3-hydroxyoxetane.